- As a child, Oprah Winfrey slept on the porch and had clothes made from potato sacks.
- She was kicked out of her home by her own people.
- After overcoming poverty, Winfrey bought one of the most expensive homes in the US and bought properties around it for nearly $50M more.
- She loves spending time on her estate with a farm, lake, wine cellar and more.
Oprah Winfrey is an eminent American television host best known for hosting the long-running talk show, "The Oprah Winfrey Show."
The TV program aired for 25 seasons from 1986 to 2011. She used the same program to talk about her weight issues.
TV host Oprah Winfrey speaks during the "The Rosie Show" panel during the OWN portion of the 2011 Summer TCA Tour at the Beverly Hilton Hotel on July 29, 2011 in Beverly Hills, California | Source: Getty Images
In 1988, she wore a pair of Calvin Klein jeans on air to show off the 67 pounds that she had shed and revealed she had "starved herself" for four months.
After the talk show ended in 2011, the 69-year-old global superstar launched her television network, the Oprah Winfrey Network (OWN).
Before becoming a renowned television presenter, Winfrey moved to Baltimore in 1976, where she hosted the TV show, "People Are Talking." She was subsequently head-hunted by a Chicago TV station to host her morning show.
Winfrey Slept on the Porch as a Child
Today, Winfrey is one of the wealthiest individuals in the world, having attained billionaire status. However, she grew up poor in harsh conditions.
The media mogul spoke candidly about her unpleasant upbringing in April 2021 and revealed it made her feel lonely. For the first six years of her life, Winfrey lived with her grandmother, Hattie Mae, in rural Mississippi. They resided on a pig farm that had scarce running water and electricity.
The pig farm where young Oprah Winfrey and her grandmother Hattie Mae lived in rural Mississippi | Source: YouTube@Smithsonian Channel
She often dressed in hessian overalls made from potato sacks and was called "Sack Girl." Winfrey also had pet cockroaches and a doll made from dried corn cob. On top of that, her grandmother consistently beat her up.
"As a young girl, I was whupped regularly," Winfrey disclosed. She explained that it was during a period when that type of treatment was acceptable because it was how kids got disciplined and sadly for her, it was common practice for her grandmother. Although the star was three then, she said she knew the mistreatment was unacceptable:
"I was beaten for the slightest reasons. Spilled water, a broken glass, the inability to keep quiet or still."
The philanthropist stated that not only did the unfortunate experience negatively affect her as a child, but it also had a long-lasting effect on her adulthood.
She became what she deemed a "world-class people pleaser" as an adult and explained it took years for her to gain enough courage to be able to say "no," confidently. The world-famous public figure noted that things would have panned out "differently" had she been cared for lovingly.
Winfrey's grandmother eventually passed, and afterward, she was "shuttled" between two cities where her parents lived separately; her mother, Vernita Lee, in Milwaukee and her father, Vernon Winfrey, in Nashville.
At age six, young Winfrey moved in with her mom and recalled being made to feel unwelcome upon arrival in Milwaukee. She explained, "The woman my mother was boarding with, Ms. Miller, took one look at me and said, 'She'll have to sleep on the porch.'"
Winfrey revealed the said Ms. Miller was Black and had a fair skin tone and could have easily been mistaken for being a White person. She refused to have who she called a "nappy-headed dark child" sleep in the same house as her.
The television producer stated her mother failed to stand up for her and readily agreed to have her sleep outside.
Lee gave birth to her daughter in Kosciusko, Mississippi, on January 29, 1954. She and her child's father only had a brief fling and were never married. Lee and Vernon were only 18 and 20 years old when they had their daughter.
Although Winfrey lived with her grandparent before, she later moved back in with her mother and endured more traumatizing experiences there.
By nine years old, family members sexually abused her, leading to her pregnancy at fourteen only to lose the child a week later.
Winfrey's mom would not have any of it and kicked her out of the house. Lee planned to take her child to a detention center, but luckily, there was not enough space to accommodate her.
Fortunately, Winfrey got sent to live with her father Vernon, who warmly welcomed her and helped her get her life back on track.
Becoming a Prominent TV Host & Finding Everlasting Love
During her rise to popularity in television, Winfrey met her longtime love, Stedman Graham, an entrepreneur. The couple crossed paths in 1986, the same year she started her beloved and now defunct chat show, "The Oprah Winfrey Show."
However, she had her guard up then because she believed he was "too handsome" and assumed he was a player. Winfrey revealed in a 1992 interview that her TV producers also felt the same way.
Oprah Winfrey and her partner Stedman Graham at the Shrine Auditorium on March 30, 1987 in Los Angeles, California | Source: Getty Images
"They figured if he looked like that, he either had to be a jerk or want something," she said. But after thinking long and hard about him becoming a potential love interest and him being single – Winfrey considered dating Graham. Thankfully, it seems it was meant to be for the lovebirds, and they have been together ever since. She gushed:
"He's kind and supportive."
Winfrey and Graham, who successfully kept their romance under wraps for decades, got engaged in 1992. At the time, she and her best friend, Gayle King, were at her home waiting on him to bring a tape from the latest episode of "The Oprah Winfrey Show."
Oprah Winfrey and Steadman Graham during the 19th Annual Daytime Emmy Awards at Sheraton Hotel on June 23, 1992 in New York City, New York | Source: Getty Images
Upon arrival, he asked for her hand in marriage instead. Winfrey boldly asked Graham whether it was the real deal, and he said he wanted her to be his wife, adding he felt it was the right time. And she answered, "Ah, that's really great."
The Hollywood power couple initially planned to exchange wedding vows the following year but never made it down the aisle. Winfrey spoke frankly about why she and Graham never got married in 2017.
She asked her significant other what he thought would have occurred if they had gone through with it, and they both concluded that they would have probably split if they had wed. The Hollywood A-lister explained:
"[..] Marriage requires a different way of being in this world."
In her 2020 "O, The Oprah Magazine letter," Winfrey admitted she grew skeptical about getting married, saying it dawned on her that marriage was not her desire. But she wanted her partner to propose because that would validate her feelings of being valued by him.
Still, she was not anticipating taking on responsibilities that make a marriage succeed because her talk show was her "priority." She and Graham were both aware of that. Winfrey divulged that her boyfriend is his own person and not merely referred to as her lover; most importantly, they share the same values.
Aside from her love life and career, Winfrey loves purchasing properties. In November 2019, she bought her neighbor actor, Jeff Bridges' Sant Barbara-area retreat, a Spanish Revival-style compound built in 1919. The acclaimed local architect James Osborne Craig initially designed the Montecito, California mansion.
Winfrey’s Enormous Montecito Home
In 2001, Winfrey bought a gigantic 23,000-square-foot Georgian-style home for a whopping $52 million. The property boasts 42 acres of land, situated in Montecito, California.
The abode was previously owned by a businessman named Robert Veloz and his spouse, Marlene, who purchased it for $14 million years earlier.
The married couple renovated the place and were not even considering selling it when Winfrey made them an offer they could not refuse.
When they eventually caved, the home deal hogged headlines as it was considered the highest-priced sale for a private home in American history then.
An exterior view of Oprah Winfrey's mega-mansion in Montecito, California | Source: YouTube@FamousEntertainment
The mansion has six bedrooms and fourteen bathrooms and features extravagant amenities, including tennis courts, an orchard, a pool, a barn, two ponds, herb and flower gardens, and a lake.
Winfrey remodeled the beachside home in 2010 and spent a fortune while at it, saying the "grand" house did not feel "true to herself."
An aerial view of Oprah Winfrey's property location in Montecito, California | Source: YouTube@FamousEntertainment
She revealed that she avoided sitting in the dining area for a decade because she did not want to ruin the "fabric" of the lavish carpet.
The actress divulged she no longer wanted a "grand space." Instead, she desired to have meaningful qualities inside the home. She admitted that although the house was stunning, it was "somewhat impersonal."
An exterior view of Oprah Winfrey's property in Montecito, California | Source: YouTube@FamousEntertainment
The two-time Oscar nominee reportedly fell in love with the abode when she used it as a backdrop for a photo shoot for her "O" magazine.
When she decided to renovate it, she hired designer Rose Tarlow to do the job and told her she felt a "disconnect" from the abode.
Pictured: Oprah Winfrey's barn at her home in Montecito, California | Source: YouTube@FamousEntertainment
Winfrey had a massive fountain almost the size of a lake and planted a forest of mature oaks. She redid the dining room, living areas, and kitchen and built a second home where she could read her newspaper while having tea. The house is an open-air stone structure she deems a "teahouse."
After completing the remodeling, the author expressed that her mansion now felt like a "womb." "It's cozy, it's styled, it's comfortable, it's me," she said.
Pictured: Oprah Winfrey's walk-in closet at her house in Montecito, California | Source: YouTube@FamousEntertainment
Renovating the property was one of many projects she had on the premises, as she expanded it over the years by purchasing adjacent estates.
Winfrey bought one neighbor's house for $4.3 million in 2004. She reportedly used the 4,584-square-foot home for housing guests.
An overview of Oprah Winfrey's vast acres of land in Montecito, California | Source: YouTube@FamousEntertainment
The TV personality made another home purchase in the same area in 2005 for a reported $7 million. The property boasts 3,376 square-foot.
That was not the end of her expansion, as in 2015, she added another 4,750-square-foot house to her portfolio. The next-door abode cost her $25 million and features four bedrooms and four-and-a-half-bathrooms.
One of Oprah Winfrey's fourteen bathrooms at her home in Montecito, California | Source: YouTube@FamousEntertainment
The sale included 23 acres of land, including a miniature pony farm. Winfrey ended up owning nearly 80 acres of property in the Montecito real estate market then.
The said mansion – which "The Color Purple" star nicknamed The Promised Land – was estimated to be valued at approximately $100 million.
Pictured: Oprah Winfrey's garden with a fountain on her property grounds in Montecito, California | Source: YouTube@FamousEntertainment
At the time, a neighbor revealed that Winfrey had been low-key and strategically buying homes surrounding her estate and was ultimately left with only one neighbor "to the west." The said neighbor stated it would not take long for her to make a move on the farm.
In a 2018 interview, Winfrey shared that she enjoyed spending her free time unproductive at her humble abode and gushed at how lovely it is and the efforts she put in to transform it into her liking.
Pictured: Oprah Winfrey's home library at her mansion in Montecito, California | Source: YouTube@FamousEntertainment
She talked about what makes her happy and provided an example of reading a book on the porch only to realize later that she gets lost in the moment.
In addition, Winfrey purchased another two-acre mansion in the neighborhood for $10.5 million but has since sold it.
Pictured: Oprah Winfrey's fish pond on her property grounds in Montecito, California | Source: YouTube@FamousEntertainment
She divided the home into two properties, including the main house, a four-bedroom, 4,320-square-foot farmhouse, and sold it to actress, Jennifer Aniston for $14.5 million.
The accompanying two smaller cottages were sold to her longtime friend and personal trainer, Bob Greene, for $2.3 million. Overall, her estate is now worth $100 million.
When discussing her home makeover, Winfrey highlighted the problematic parts of transforming one of the spaces inside. "It's not easy to do an entire library that says, 'Do not touch the books.'"
However, she succeeded in getting it right and expressed how much words mean to her; hence she decided to "incorporate" them in most of the rooms in her house.
Winfrey also talked about having some friends over and said they usually wind up in the kitchen, which she loves because she enjoys spending time there.
That said, she revealed that she would create more space in the room by doing away with the pizza oven and the fireplace, adding the rest of the pieces would remain intact.
Winfrey's home has six bedrooms, fourteen bathrooms, and ten fireplaces, including a gourmet kitchen, two theatres, a wine cellar, a barn, an outdoor entertainment area, and a massive guesthouse with a pool.
Montecito is a picturesque and secluded region on the south coast of Santa Barbara County. It is a wine country with some of the highest-priced wines in the Santa Barbara landscape. The climate has been described as Mediterranean, which is a tourist attraction and is perfect for gardening.
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